| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| Other Sizes |
| Targets |
The primary molecular targets of (S)-(-)-5-Fluorowillardiine are the AMPA (α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid) subtype of ionotropic glutamate receptors. It acts as a potent agonist, directly activating these receptors . The compound exhibits significant subunit selectivity, showing high affinity for subunits GluR1 (Kd ~3-4 nM) and GluR2 (Kd ~7-12 nM), while displaying lower affinity for GluR3 and GluR4 subunits (Kd ~150-800 nM) . The activation of AMPA receptors by (S)-(-)-5-Fluorowillardiine leads to sodium and calcium ion influx, resulting in neuronal depolarization and downstream signaling events.
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| ln Vitro |
In vitro studies have demonstrated that (S)-(-)-5-Fluorowillardiine is a more potent AMPA receptor agonist than AMPA itself. Its binding affinity (Ki) values are 14.7 nM for human GluR1, 25.1 nM for human GluR2, and 1820 nM for human GluR5 . Radioligand binding studies using [³H]Fluorowillardiine in rat brain membranes revealed two affinity components: a high-affinity site with a Kd of approximately 20 nM and a low-affinity site with a Kd of approximately 1 μM, with low-affinity sites accounting for about 90% of all binding sites . The compound's binding is greatly skewed in favor of GluR1 and GluR2 subunits due to its subunit preference, making it a valuable tool for studying AMPA receptor composition and pharmacology .
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| ln Vivo |
(S)-(-)-5-Fluorowillardiine is identified as an excitotoxic neurotoxin when used in vivo, which consequently limits its application in intact animal studies . Because of this toxicity, it is rarely used in living animal models for therapeutic or functional studies. Its primary value lies in its application as a precise pharmacological probe to selectively stimulate AMPA receptors in isolated tissue preparations or in vitro systems . As a discovery agent, it remains an investigative tool rather than a therapeutic candidate .
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| Enzyme Assay |
Binding assays for (S)-(-)-5-Fluorowillardiine are typically performed using rat brain membrane preparations or recombinant homomeric AMPA receptors expressed in HEK293 cells . A standard saturation binding protocol involves incubating membranes with varying concentrations of [³H]Fluorowillardiine (e.g., 3–2000 nM) for 60 minutes at 25°C (or at 0°C) . Incubations are terminated by centrifugation, followed by rinsing of membrane pellets. The pellets are then dissolved, and radioactivity is measured by scintillation counting . Nonspecific binding is determined in the presence of 5 mM L-glutamate. Data analysis is performed using nonlinear regression to determine Kd and Bmax values . For competition binding experiments, displacement of [³H]CNQX (40 nM) by unlabeled Fluorowillardiine is measured under similar conditions .
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| Cell Assay |
Cellular assays using (S)-(-)-5-Fluorowillardiine are primarily conducted as binding studies on cell membrane preparations rather than functional cell viability or signaling assays . A representative protocol for studies on recombinant homomeric AMPA receptors (GluR1-4) expressed in HEK293 cells is as follows: Permeabilized cells are incubated with [³H]Fluorowillardiine at 0°C . Binding is terminated by filtration through glass fiber filters, followed by rapid washing with chilled buffer containing thiocyanate to minimize ligand dissociation. Nonspecific binding is defined with 5 mM glutamate . The compound is not typically used in standard cytotoxicity or proliferation assays but rather as a radioligand for receptor occupancy studies.
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| Animal Protocol |
Due to its identified excitotoxic neurotoxicity, this compound is rarely, if ever, used in intact animal models for therapeutic or pharmacodynamic evaluation . Its usage is virtually exclusive to in vitro preparations designed to study AMPA receptor function in isolated systems, such as brain slices or primary neuronal cultures. Consequently, no analgesic, anti-cancer, or other therapeutic efficacy data from animal models is available for this compound.
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| ADME/Pharmacokinetics |
As a research tool compound and not a therapeutic candidate, detailed ADME (Absorption, Distribution, Metabolism, Excretion) profiling has not been performed. Its physicochemical properties have been computationally predicted: LogP value is -1.54, and LogD (pH 7.4) is -4.26, indicating high hydrophilicity . The polar surface area is 113 Ų . The compound has a molecular weight of 217.15 g/mol and follows Lipinski's Rule of 5 with one violation .
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| Toxicity/Toxicokinetics |
The primary recognized toxicity of (S)-(-)-5-Fluorowillardiine is its excitotoxic neurotoxicity . As a potent AMPA receptor agonist, excessive receptor activation can lead to neuronal cell death via excitotoxic mechanisms, involving calcium overload and downstream degenerative pathways. This property is the principal limitation for its use in living animals. No specific data on acute toxicity (LD50), chronic toxicity, genotoxicity, or reproductive toxicity is available in standard pharmacological databases. The compound is classified as an investigative discovery agent and is strictly intended for research use only, not for human therapeutic or diagnostic applications .
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| References |
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| Molecular Formula |
C7H9CLFN3O4
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|---|---|
| Molecular Weight |
253.6155
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| Exact Mass |
253.026
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| CAS # |
1321546-70-6
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| Related CAS # |
(S)-(-)-5-Fluorowillardiine;140187-23-1
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| PubChem CID |
92044399
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| Appearance |
White to off-white solid powder
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
16
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| Complexity |
354
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C1=C(C(=O)NC(=O)N1C[C@@H](C(=O)O)N)F.Cl
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| InChi Key |
TXWOAFHJFQTAEW-WCCKRBBISA-N
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| InChi Code |
InChI=1S/C7H8FN3O4.ClH/c8-3-1-11(2-4(9)6(13)14)7(15)10-5(3)12;/h1,4H,2,9H2,(H,13,14)(H,10,12,15);1H/t4-;/m0./s1
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| Chemical Name |
(2S)-2-amino-3-(5-fluoro-2,4-dioxopyrimidin-1-yl)propanoic acid;hydrochloride
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ~6.67 mg/mL (~26.30 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.9429 mL | 19.7145 mL | 39.4291 mL | |
| 5 mM | 0.7886 mL | 3.9429 mL | 7.8858 mL | |
| 10 mM | 0.3943 mL | 1.9715 mL | 3.9429 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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